How We Booked a $20,000 Vacation With Points

#289: Chris and Amy booked a last-minute week in Bora Bora that would have cost over $20,000, almost entirely on points. They break down how it came together, why they chose Bora Bora over Fiji, the Marriott award search quirk that hid available rooms, flying business class in both directions by mixing two airlines, and using card travel credits on the inter-island flights. Then, three nights in, they decided to abandon the deal and pay more to switch resorts. They compare and rank the major Bora Bora resorts, weigh points versus cash, and explain what makes French Polynesia one of the easiest long-haul trips from the West Coast.Link to Full Show Notes: https://chrishutchins.com/bora-bora-on-points-2026/Partner DealsHaven: Skip the waitlist for the best sauna.Gelt: ⁠Skip the waitlist on personalized tax guidance to maximize your wealthThrive Market: ⁠30% off your first order of organic groceries + a free $60 giftBilt Rewards: ⁠Earn the most valuable points when you pay rentSuperhuman: ⁠Free month of the fastest and best email with code ALLTHEHACKSFor all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/dealsResources MentionedHotels & ResortsHotel Upgrade ProgramThe Westin Bora Bora Resort & SpaFour Seasons Resort Bora BoraThe St. Regis Bora Bora ResortConrad Bora Bora NuiThe BrandoLe Taha'aNanuku ResortWaldorf Astoria Costa RicaProductsMonopoly DealHealth & Sauna ResearchBryan Johnson — Is Sauna ACTUALLY Good For You? (90-Day Experiment)ATH Podcast#285: Why Net Fulfillment Beats Net Worth with Bill Perkins#287: Putting Die With Zero Into Practice with Brad BarrettHotel Upgrade ProgramBest Cards PageGift Cards PageNewsletterAMA: Submit QuestionsLeave a review: Apple Podcasts | SpotifyEmail for questions, hacks, deals, and feedback: [email protected] Show Notes(00:00) Introduction(02:09) How a Kid-Free Trip Came Together(03:33) How Chris and Amy Choose Vacation Destinations(13:09) Why French Polynesia Over Fiji(14:59) Booking The Westin(20:43) Flying Business Class Both Ways on Two Different Airlines(26:22) Air Tahiti Nui and the Inter-Island Flights(31:15) A Surprise First Class Upgrade on Air Moana(32:47) Arriving in Bora Bora and Checking Into The Westin(34:29) First Impressions: A Brand-New Property with Great Bones(37:33) A Thousand Little Cuts: The Westin's Service Problems(44:50) The Math Behind Checking Out Early (52:21) The Four Seasons vs. The Westin: What the Extra Money Buys(59:23) Why the Four Seasons Spa Facilities Stood Out(01:00:37) Getting Serious About Sauna Again(01:05:51) Pickleball, Paddleboarding, and Space to Get Lost(01:08:00) Did the Four Seasons Save the Trip?(01:13:18) How to Actually Get Deals at the Four Seasons(01:16:20) Ranking All Four Bora Bora Resorts(01:19:32) Why Fiji Is Still at the Top of the List(01:21:45) Where AI Can Go Wrong(01:23:15) Packing a Travel Med Bag for Remote Destinations(01:24:20) Final Thoughts and Why Bora Bora Keeps WinningConnect with Chris⁠⁠Newsletter⁠⁠ | ⁠Membership⁠⁠ | ⁠X⁠⁠ | ⁠Instagram⁠⁠ | ⁠LinkedIn⁠⁠Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.